(11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester

Base Information

• Chemical Name: (11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester
• CAS No.: 221633-52-9
• Molecular Formula: C₁₉H₃₂O₄
• Molecular Weight: 324.461
• Mol file: 221633-52-9.mol

Synonyms:

Chemical Property of (11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester

There total 22 articles about (11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(Z)-3-Hexen-1-ol (928-96-1) → (11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester (221633-52-9)

Guidance literature:

Multi-step reaction with 15 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

2: n-BuLi / hexane; tetrahydrofuran / 2 h / 0 °C

3: 89 percent / DIBAL-H / diethyl ether / 1 h / 0 °C

4: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

5: 83 percent / n-BuLi, HMPA / tetrahydrofuran; hexane / 1.) 0 deg C, 1 h, 2.) 0 deg C, 1 h

6: 96 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

7: 96 percent / TBAF / tetrahydrofuran / 2 h / 0 °C

8: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

9: 98 percent / 2-methylbut-2-ene, sodium dihydrogen phosphate, sodium chlorite / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

10: 99 percent / K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

11: 98 percent / K₂CO₃ / methanol / 4 h / 0 °C

12: 99 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

13: 96 percent / pyridine, H₂ / Pd/CaCO₃ / hexane / 7 h / Ambient temperature

14: 97 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

15: 1.) 3 Angstroem molecular sieves, CaH₂, Ti(O-iPr)4, Li-(+)-diisopropyl tartrate, 2.) t-BuOOH / 1.) CH₂Cl₂, -20 deg C, 1 h, 2.) 2,2,4-trimethylpentane, CH₂Cl₂, -20 deg C, 24 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; n-butyllithium; calcium hydride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; Li (+)-diisopropyl tartrate; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield:

(3Z)-hexenal (6789-80-6) → (11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester (221633-52-9)

Guidance literature:

Multi-step reaction with 14 steps

1: n-BuLi / hexane; tetrahydrofuran / 2 h / 0 °C

2: 89 percent / DIBAL-H / diethyl ether / 1 h / 0 °C

3: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

4: 83 percent / n-BuLi, HMPA / tetrahydrofuran; hexane / 1.) 0 deg C, 1 h, 2.) 0 deg C, 1 h

5: 96 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

6: 96 percent / TBAF / tetrahydrofuran / 2 h / 0 °C

7: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

8: 98 percent / 2-methylbut-2-ene, sodium dihydrogen phosphate, sodium chlorite / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

9: 99 percent / K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

10: 98 percent / K₂CO₃ / methanol / 4 h / 0 °C

11: 99 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

12: 96 percent / pyridine, H₂ / Pd/CaCO₃ / hexane / 7 h / Ambient temperature

13: 97 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

14: 1.) 3 Angstroem molecular sieves, CaH₂, Ti(O-iPr)4, Li-(+)-diisopropyl tartrate, 2.) t-BuOOH / 1.) CH₂Cl₂, -20 deg C, 1 h, 2.) 2,2,4-trimethylpentane, CH₂Cl₂, -20 deg C, 24 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; n-butyllithium; calcium hydride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; Li (+)-diisopropyl tartrate; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield:

(2E,5Z)-Octa-2,5-dien-1-ol (67548-36-1,83861-75-0) → (11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester (221633-52-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

2: 83 percent / n-BuLi, HMPA / tetrahydrofuran; hexane / 1.) 0 deg C, 1 h, 2.) 0 deg C, 1 h

3: 96 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

4: 96 percent / TBAF / tetrahydrofuran / 2 h / 0 °C

5: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

6: 98 percent / 2-methylbut-2-ene, sodium dihydrogen phosphate, sodium chlorite / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

7: 99 percent / K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

8: 98 percent / K₂CO₃ / methanol / 4 h / 0 °C

9: 99 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

10: 96 percent / pyridine, H₂ / Pd/CaCO₃ / hexane / 7 h / Ambient temperature

11: 97 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

12: 1.) 3 Angstroem molecular sieves, CaH₂, Ti(O-iPr)4, Li-(+)-diisopropyl tartrate, 2.) t-BuOOH / 1.) CH₂Cl₂, -20 deg C, 1 h, 2.) 2,2,4-trimethylpentane, CH₂Cl₂, -20 deg C, 24 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; n-butyllithium; calcium hydride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; Li (+)-diisopropyl tartrate; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; Dess-Martin periodane; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

upstream raw materials:

methanol

(Z)-10-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester

(9Z,12E,15Z)-11-Hydroxyoctadeca-9,12,15-trienoic acid methyl ester

(Z)-3-Hexen-1-ol